Ethyl 4-iso-butylbenzoylformate → 4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone

HRID 369153Notes

Reaction equation

HRID 369153 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([C:13]1[CH:25]=[CH:24][C:16]([C:17]([C:19]([O:21]CC)=O)=[O:18])=[CH:15][CH:14]=1)[CH:10]([CH3:12])[CH3:11].[OH:26][C:27]1[C:28](=O)[O:29][C:30](C)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)C=1O>C1COCC1>[OH:21][C:19]1[C:17]([C:16]2[CH:15]=[CH:14][C:13]([CH2:9][CH:10]([CH3:11])[CH3:12])=[CH:25][CH:24]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:18][C:27](=[O:26])[C:28]=1[O:29][CH2:30][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 12585534Ethyl 4-iso-butylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 547235924-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanoneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 3.5 mL (10.5 mmol) of 3.0M phenylmagnesium bromide was added to a solution of 2.3 g (10 mmol) of ethyl 4-isobutylbenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provide an oil, which was purified over 400 g of SiO2 by eluting with 5000 mL of CHCl3, 500 mL of EtOH/CHCl3 (3/97) and 500 mL of EtOH/CHCl3 (8/92) to provide 1.2 g (29% yield) of 4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone as a tan powder recrystallized from CHCl3 and hexanes.

Workup

  1. customto provide an oil, which
  2. customwas purified over 400 g of SiO2
  3. washby eluting with 5000 mL of CHCl3, 500 mL of EtOH/CHCl3 (3/97) and 500 mL of EtOH/CHCl3 (8/92)

Sources & evidence

ORD record
ord-6e2d0472aaee40ef96002bbc108b36d3
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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